Chapter 9. Nuclear Magnetic Resonance. Ch. 9-1
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1 Chapter 9 Nuclear Magnetic Resonance Ch. 9-1
2 1. Introduction Classic methods for organic structure determination Boiling point Refractive index Solubility tests Functional group tests Derivative preparation Sodium fusion (to identify N, Cl, Br, I & S) Mixture melting point Combustion analysis Degradation Ch. 9-2
3 Classic methods for organic structure determination Require large quantities of sample and are time consuming Ch. 9-3
4 Spectroscopic methods for organic structure determination a) Mass Spectroscopy (MS) Molecular Mass & characteristic fragmentation pattern b) Infrared Spectroscopy (IR) Characteristic functional groups c) Ultraviolet Spectroscopy (UV) Characteristic chromophore d) Nuclear Magnetic Resonance (NMR) Ch. 9-4
5 Spectroscopic methods for organic structure determination Combination of these spectroscopic techniques provides a rapid, accurate and powerful tool for Identification and Structure Elucidation of organic compounds Rapid Effective in mg and microgram quantities Ch. 9-5
6 General steps for structure elucidation 1. Elemental analysis Empirical formula e.g. C 2 4 O 2. Mass spectroscopy Molecular weight Molecular formula e.g. C 4 8 O 2, C 6 12 O 3 etc. Characteristic fragmentation pattern for certain functional groups Ch. 9-6
7 General steps for structure elucidation 3. From molecular formula Double bond equivalent (DBE) 4. Infrared spectroscopy (IR) Identify some specific functional groups e.g. C=O, C O, O, COO, N 2 etc. Ch. 9-7
8 General steps for structure elucidation 5. UV Sometimes useful especially for conjugated systems e.g. dienes, aromatics, enones 6. 1, 13 C NMR and other advanced NMR techniques Full structure determination Ch. 9-8
9 Electromagnetic spectrum cosmic & γ-rays X-rays ultraviolet visible infrared microwave radiowave λ: 0.1nm 200nm 400nm 800nm 50µm X-Ray Crystallography UV IR NMR 1Å = m 1nm = 10-9 m 1µm = 10-6 m Ch. 9-9
10 2. Nuclear Magnetic Resonance (NMR) Spectroscopy A graph that shows the characteristic energy absorption frequencies and intensities for a sample in a magnetic field is called a nuclear magnetic resonance (NMR) spectrum Ch. 9-10
11 Ch. 9-11
12 1. The number of signals in the spectrum tells us how many different sets of protons there are in the molecule 2. The position of the signals in the spectrum along the x-axis tells us about the magnetic environment of each set of protons arising largely from the electron density in their environment Ch. 9-12
13 3. The area under the signal tells us about how many protons there are in the set being measured 4. The multiplicity (or splitting pattern) of each signal tells us about the number of protons on atoms adjacent to the one whose signal is being measured Ch. 9-13
14 Typical 1 NMR spectrum Chemical Shift (δ) Integration (areas of peaks no. of ) Multiplicity (spin-spin splitting) and coupling constant Ch. 9-14
15 Typical 1 NMR spectrum Record as: 1 NMR (300 Mz, CDCl 3 ): δ 4.35 (2, t, J = 7.2 z, c ) 2.05 (2, sextet, J = 7.2 z, b ) 1.02 (3, t, J = 7.2 z, a ) chemical shift (δ) in ppm no. of (integration) multiplicity coupling constant in z Ch. 9-15
16 2A. Chemical Shift The position of a signal along the x-axis of an NMR spectrum is called its chemical shift The chemical shift of each signal gives information about the structural environment of the nuclei producing that signal Counting the number of signals in a 1 NMR spectrum indicates, at a first approximation, the number of distinct proton environments in a molecule Ch. 9-16
17 Ch. 9-17
18 Ch. 9-18
19 Normal range of 1 NMR "upfield" (more shielded) "downfield" (deshielded) δ ppm (low field strength) (high field strength) Ch. 9-19
20 Reference compound TMS = tetramethylsilane Me Me Si Me as a reference standard (0 ppm) Me Reasons for the choice of TMS as reference Resonance position at higher field than other organic compounds Unreactive and stable, not toxic Volatile and easily removed (B.P. = 28 o C) Ch. 9-20
21 NMR solvent Normal NMR solvents should not contain hydrogen Common solvents CDCl 3 C 6 D 6 CD 3 OD CD 3 COCD 3 (d 6 -acetone) Ch. 9-21
22 The 300-Mz 1 NMR spectrum of 1,4-dimethylbenzene Ch. 9-22
23 2B. Integration of Signal Areas Integral Step eights The area under each signal in a 1 NMR spectrum is proportional to the number of hydrogen atoms producing that signal It is signal area (integration), not signal height, that gives information about the number of hydrogen atoms Ch. 9-23
24 a a b R O b b 2 a 3 b b a Ch. 9-24
25 2C. Coupling (Signal Splitting) Coupling is caused by the magnetic effect of nonequivalent hydrogen atoms that are within 2 or 3 bonds of the hydrogens producing the signal The n+1 rule Rule of Multiplicity: If a proton (or a set of magnetically equivalent nuclei) has n neighbors of magnetically equivalent protons. It s multiplicity is n + 1 Ch. 9-25
26 Examples (1) b a b C C Cl b a a : multiplicity = = 4 (a quartet) b : multiplicity = = 3 (a triplet) (2) a b Cl C C Cl Cl b a : multiplicity = = 3 (a triplet) b : multiplicity = = 2 (a doublet) Ch. 9-26
27 Ch. 9-27
28 Examples (3) b a b C C Br b b b b a : multiplicity = = 7 (a septet) b : multiplicity = = 2 (a doublet) Note: All b s are chemically and magnetically equivalent. Ch. 9-28
29 Pascal s Triangle Use to predict relative intensity of various peaks in multiplet Given by the coefficient of binomial expansion (a + b) n singlet (s) 1 doublet (d) 1 1 triplet (t) quartet (q) quintet sextet Ch. 9-29
30 Pascal s Triangle For For a b Br C C Br Cl Cl a b Cl C C Br Cl Br Due to symmetry, a and b are identical a singlet a b two doublets Ch. 9-30
31 3. ow to Interpret Proton NMR Spectra 1. Count the number of signals to determine how many distinct proton environments are in the molecule (neglecting, for the time being, the possibility of overlapping signals) 2. Use chemical shift tables or charts to correlate chemical shifts with possible structural environments Ch. 9-31
32 3. Determine the relative area of each signal, as compared with the area of other signals, as an indication of the relative number of protons producing the signal 4. Interpret the splitting pattern for each signal to determine how many hydrogen atoms are present on carbon atoms adjacent to those producing the signal and sketch possible molecular fragments 5. Join the fragments to make a molecule in a fashion that is consistent with the data Ch. 9-32
33 Example: 1 NMR (300 Mz) of an unknown compound with molecular formula C 3 7 Br Ch. 9-33
34 Three distinct signals at ~ δ3.4, 1.8 and 1.1 ppm δ3.4 ppm: likely to be near an electronegative group (Br) Ch. 9-34
35 δ (ppm): Integral: Ch. 9-35
36 δ (ppm): Multiplicity: triplet sextet triplet 2 's on adjacent C 5 's on adjacent C 2 's on adjacent C Ch. 9-36
37 Complete structure: most downfield signal Br C 2 C 2 C 3 most upfield signal 2 's from integration triplet 2 's from integration sextet 3 's from integration triplet Ch. 9-37
38 4. Nuclear Spin: The Origin of the Signal The magnetic field associated with a spinning proton The spinning proton resembles a tiny bar magnet Ch. 9-38
39 Ch. 9-39
40 Ch. 9-40
41 Spin quantum number (I) 1 : I = ½ (two spin states: +½ or -½) (similar for 13 C, 19 F, 31 P) 12 C, 16 O, 32 S: I = 0 These nuclei do not give an NMR spectrum Ch. 9-41
42 5. Detecting the Signal: Fourier Transform NMR Spectrometers Ch. 9-42
43 Ch. 9-43
44 6. Shielding & Deshielding of Protons All protons do not absorb energy at the same frequency in a given external magnetic field Lower chemical shift values correspond with lower frequency igher chemical shift values correspond with higher frequency "upfield" (more shielded) "downfield" (deshielded) (low field δ ppm (high field strength) strength) Ch. 9-44
45 Ch. 9-45
46 Deshielding by electronegative groups C 3 X X = F O Cl Br I Electronegativity δ (ppm) Greater electronegativity Deshielding of the proton Larger δ Ch. 9-46
47 Shielding and deshielding by circulation of π electrons If we were to consider only the relative electronegativities of carbon in its three hybridization states, we might expect the following order of protons attached to each type of carbon: (higher frequency) sp < sp2 < sp 3 (lower frequency) Ch. 9-47
48 In fact, protons of terminal alkynes absorb between δ 2.0 and δ 3.0, and the order is (higher frequency) sp2 < sp < sp 3 (lower frequency) Ch. 9-48
49 This upfield shift (lower frequency) of the absorption of protons of terminal alkynes is a result of shielding produced by the circulating π electrons of the triple bond Shielded (δ 2 3 ppm) Ch. 9-49
50 Aromatic system Shielded region Deshielded region Ch. 9-50
51 e.g. d c a b δ (ppm) a & b : 7.9 & 7.4 (deshielded) c & d : (shielded) Ch. 9-51
52 Alkenes Deshielded (δ ppm) Ch. 9-52
53 Aldehydes R O Electronegativity effect + Anisotropy effect δ = ppm (deshielded) Ch. 9-53
54 7. The Chemical Shift Reference compound TMS = tetramethylsilane Me Me as a reference standard (0 ppm) Reasons for the choice of TMS as reference Resonance position at higher field than other organic compounds Unreactive and stable, not toxic Volatile and easily removed (B.P. = 28 o C) Si Me Me Ch. 9-54
55 7A. PPM and the δ Scale The chemical shift of a proton, when expressed in hertz (z), is proportional to the strength of the external magnetic field Since spectrometers with different magnetic field strengths are commonly used, it is desirable to express chemical shifts in a form that is independent of the strength of the external field Ch. 9-55
56 Since chemical shifts are always very small (typically 5000 z) compared with the total field strength (commonly the equivalent of 60, 300, or 600 million hertz), it is convenient to express these fractions in units of parts per million (ppm) This is the origin of the delta scale for the expression of chemical shifts relative to TMS δ = (observed shift from TMS in hertz) x 10 6 (operating frequency of the instrument in hertz) Ch. 9-56
57 For example, the chemical shift for benzene protons is 2181 z when the instrument is operating at 300 Mz. Therefore δ = The chemical shift of benzene protons in a 60 Mz instrument is 436 z: δ = 2181 z x x 10 6 z 436 z x x 10 6 z = 7.27 ppm = 7.27 ppm Thus, the chemical shift expressed in ppm is the same whether measured with an instrument operating at 300 or 60 Mz (or any other field strength) Ch. 9-57
58 8. Chemical Shift Equivalent and Nonequivalent Protons Two or more protons that are in identical environments have the same chemical shift and, therefore, give only one 1 NMR signal Chemically equivalent protons are chemical shift equivalent in 1 NMR spectra Ch. 9-58
59 8A. omotopic and eterotopic Atoms If replacing the hydrogens by a different atom gives the same compound, the hydrogens are said to be homotopic omotopic hydrogens have identical environments and will have the same chemical shift. They are said to be chemical shift equivalent Ch. 9-59
60 same compounds Br Br C C C Br C C C C C Ethane The six hydrogens of ethane are homotopic and are, therefore, chemical shift equivalent Ethane, consequently, gives only one signal in its 1 NMR spectrum C C C Br C C C Br Br same compounds Ch. 9-60
61 If replacing hydrogens by a different atom gives different compounds, the hydrogens are said to be heterotopic eterotopic atoms have different chemical shifts and are not chemical shift equivalent Ch. 9-61
62 same compounds these 3 s of the C 3 group are homotopic the C 3 group gives only one 1 NMR signal Cl Cl C C C Cl Br C Br C Br C C Br C C Br C C These 2 s are also homotopic to each other Br C Cl Cl different compounds heterotopic Ch. 9-62
63 Br C C C 3 C 2 Br two sets of hydrogens that are heterotopic with respect to each other two 1 NMR signals Ch. 9-63
64 Other examples (1) C C C 3 C NMR signals C 3 (2) 4 1 NMR signals C 3 Ch. 9-64
65 Other examples (3) 3 C C NMR signals Ch. 9-65
66 Application to 13 C NMR spectroscopy Examples (1) 3 C C C NMR signal C 3 (2) C C NMR signals Ch. 9-66
67 (3) 5 13 C NMR signals O O (4) O 4 13 C NMR signals O Ch. 9-67
68 8B. Enantiotopic and Diastereotopic ydrogen Atoms If replacement of each of two hydrogen atoms by the same group yields compounds that are enantiomers, the two hydrogen atoms are said to be enantiotopic Ch. 9-68
69 Enantiotopic hydrogen atoms have the same chemical shift and give only one 1 NMR signal: enantiotopic 3 C G Br 3 C Br enantiomer G 3 C Br Ch. 9-69
70 3 C b chirality centre a O C 3 diastereotopic 3 C b 3 C G G a O C 3 O C 3 diastereomers Ch. 9-70
71 G Br a b diastereotopic Br Br a b G diastereomers Ch. 9-71
72 9. Signal Splitting: Spin Spin Coupling Vicinal coupling is coupling between hydrogen atoms on adjacent carbons (vicinal hydrogens), where separation between the hydrogens is by three σ bonds a b 3 J or vicinal coupling Ch. 9-72
73 9A. Vicinal Coupling Vicinal coupling between heterotopic protons generally follows the n + 1 rule. Exceptions to the n + 1 rule can occur when diastereotopic hydrogens or conformationally restricted systems are involved Signal splitting is not observed for protons that are homotopic (chemical shift equivalent) or enantiotopic Ch. 9-73
74 9B. Splitting Tree Diagrams and the Origin of Signal Splitting Splitting analysis for a doublet b C a C Ch. 9-74
75 Splitting analysis for a triplet b C b a C b a b C C C Ch. 9-75
76 Splitting analysis for a quartet b b C b a C Ch. 9-76
77 Pascal s Triangle Use to predict relative intensity of various peaks in multiplet Given by the coefficient of binomial expansion (a + b) n singlet (s) 1 doublet (d) 1 1 triplet (t) quartet (q) quintet sextet Ch. 9-77
78 9C. Coupling Constants Recognizing Splitting Patterns a b X C C b a b Ch. 9-78
79 9D. The Dependence of Coupling Constants on Dihedral Angle 3 J values are related to the dihedral angle (φ) φ Ch. 9-79
80 Karplus curve φ ~0 o or 180 o Maximum 3 J value φ ~90 o 3 J ~0 z Ch. 9-80
81 Karplus curve Examples b b a (axial, axial) a φ = 180º J a,b = z a b φ = 60º J a,b = 4-5 z b a (equatorial, equatorial) Ch. 9-81
82 Karplus curve Examples b a (equatorial, axial) b a φ = 60º J a,b = 4-5 z Ch. 9-82
83 9E. Complicating Features The 60 Mz 1 NMR spectrum of ethyl chloroacetate Ch. 9-83
84 The 300 Mz 1 NMR spectrum of ethyl chloroacetate Ch. 9-84
85 9F. Analysis of Complex Interactions Ch. 9-85
86 The 300 Mz 1 NMR spectrum of 1- nitropropane Ch. 9-86
87 10. Proton NMR Spectra and Rate Processes Protons of alcohols (RO) and amines may appear over a wide range from ppm ydrogen-bonding is the reason for this range in high dilution (free O): R O δ = ~ ppm in conc. solution (-bonded): R δ R O O δ + O R proton more deshielded Ch. 9-87
88 Why don t we see coupling with the O proton, e.g. C 2 O (triplet?) Because the acidic protons are exchangeable about 10 5 protons per second (residence time 10-5 sec), but the NMR experiment requires a time of sec. to take a spectrum, usually we just see an average (thus, O protons are usually a broad singlet) Ch. 9-88
89 Trick: Run NMR in d -DMSO where - 6 bonding with DMSO s oxygen prevents s from exchanging and we may be able to see the coupling Ch. 9-89
90 Deuterium Exchange To determine which signal in the NMR spectrum is the O proton, shake the NMR sample with a drop of D O and whichever peak 2 disappears that is the O peak (note: a new peak of OD appears) D 2 O R O R O D + OD Ch. 9-90
91 Phenols Phenol protons appear downfield at 4-7 ppm They are more acidic - more + character More dilute solutions - peak appears upfield: towards 4 ppm O O Ch. 9-91
92 Phenols Intramolecular -bonding causes downfield shift O O 12.1 ppm Ch. 9-92
93 11. Carbon-13 NMR Spectroscopy 11A. Interpretation of 13 C NMR Spectra Unlike 1 with natural abundance ~99.98%, only 1.1% of carbon, namely 13 C, is NMR active Ch. 9-93
94 11B. One Peak for Each Magnetically Distinct Carbon Atom 13 C NMR spectra have only become commonplace more recently with the introduction of the Fourier Transform (FT) technique, where averaging of many scans is possible (note 13 C spectra are 6000 times weaker than 1 spectra, thus require a lot more scans for a good spectrum) Ch. 9-94
95 Note for a 200 Mz NMR (field strength 4.70 Tesla) 1 NMR Frequency = 200 Mz 13 C NMR Frequency = 50 Mz Ch. 9-95
96 Example: 2-Butanol C 3 C C 2 C 3 O Proton-coupled 13 C NMR spectrum Ch. 9-96
97 Example: 2-Butanol C 3 C C 2 C 3 O Proton-decoupled 13 C NMR spectrum Ch. 9-97
98 11C. 13 C Chemical Shifts Decreased electron density around an atom deshields the atom from the magnetic field and causes its signal to occur further downfield (higher ppm, to the left) in the NMR spectrum Relatively higher electron density around an atom shields the atom from the magnetic field and causes the signal to occur upfield (lower ppm, to the right) in the NMR spectrum Ch. 9-98
99 Factors affecting chemical shift i. Diamagnetic shielding due to bonding ii. iii. electrons Paramagnetic shielding due to low-lying electronic excited state Magnetic Anisotropy through space due to the near-by group (especially π electrons) In 1 NMR, (i) and (iii) most significant; in 13 C NMR, (ii) most significant (since chemical shift range >> 1 NMR) Ch. 9-99
100 Electronegative substituents cause downfield shift Increase in relative atomic mass of substituent causes upfield shift X Electronegativity Atomic Mass 13 C NMR: C 3 X Cl ppm Br ppm I ppm Ch
101 ybridization of carbon sp 2 > sp > sp 3 e.g. 2 C C 2 C C 3 C C ppm 71.9 ppm 5.7 ppm Ch
102 Anisotropy effect Shows shifts similar to the effect e.g. in 1 NMR C C C shows large upfield shift Ch
103 Ch
104 Ch
105 (a) (b) (c) Cl C 2 C C 3 O 1-Chloro-2-propanol (b) (a) (c) Ch
106 11D. Off-Resonance Decoupled Spectra NMR spectrometers can differentiate among carbon atoms on the basis of the number of hydrogen atoms that are attached to each carbon In an off-resonance decoupled 13 C NMR spectrum, each carbon signal is split into a multiplet of peaks, depending on how many hydrogens are attached to that carbon. An n + 1 rule applies, where n is the number of hydrogens on the carbon in question. Thus, a carbon with no hydrogens produces a singlet (n = 0), a carbon with one hydrogen produces a doublet (two peaks), a carbon with two hydrogens produces a triplet (three peaks), and a methyl group carbon produces a quartet (four peaks) Ch
107 Off-resonance decoupled 13 C NMR 1 2 N O N Broadband proton-decoupled 13 C NMR Ch
108 11E. DEPT 13 C Spectra DEPT 13 C NMR spectra indicate how many hydrogen atoms are bonded to each carbon, while also providing the chemical shift information contained in a broadband proton-decoupled 13 C NMR spectrum. The carbon signals in a DEPT spectrum are classified as C 3, C 2, C, or C accordingly Ch
109 (a) (b) (c) (b) (a) (c) Cl C 2 C C 3 O 1-Chloro-2-propanol Ch
110 The broadband proton-decoupled 13 C NMR spectrum of methyl methacrylate Ch
111 12. Two-Dimensional (2D) NMR Techniques COSY 1 1 correlation spectroscopy ETCOR eteronuclear correlation spectroscopy Ch
112 COSY of 2-chloro-butane Ch
113 ETCOR of 2-chloro-butane C 3 C 1 C 4 C Ch
114 END OF CAPTER 9 Ch
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